


Learning from a Date

by orphan_account



Category: Supernatural
Genre: F/M, Language, slight angst
Language: English
Status: Completed
Published: 2018-12-18
Updated: 2018-12-18
Packaged: 2019-09-22 10:50:40
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,363
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17058404
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: In an attempt to take your mind off your unrequited love for Dean Winchester, you decide to teach Castiel what it is like to go on a date.  But when Dean hears about it, things go according to plan…at least Sam and Cas’ plan.





	Learning from a Date

It’s been your experience that there are two types of hunters.  One is like Dean Winchester.  Hardened.  Badass.  Always does what has to be done, no matter the cost, to save the people.  But mainly the word to focus on is badass.  The second kind is more like Garth.  A sweetheart.  Yea, they are great hunters, but right at their core, you can’t out love their kindness.  They don’t just do a job, they make sure everyone is safe, make sure everyone is comforted.  And they do it all with a smile on their face. 

 

So there you have it, the badasses and the sweethearts.  You…you were a sweetheart, which was why you were so easily persuaded to help out a friend…

 

You had been hunting with the boys for a few years now.  You found them on a hunt for a rouge vampire.  You had been tracking it for months, but the guys found it in a few days, which irritated you to no end.  And of course, you fell for that Winchester charm, and when they asked you to join up with the team, you didn’t hesitate to say yes.  Part of you thought, it was a good thought.  Bigger team, safer to hunt that way.  Another part of you, the one you knew had a larger control over you, knew you would have said yes to anything that green eyed man had asked you.

 

Oh yes, you had it bad for Dean Winchester.  And in all the years you had known him, you had thrown out so many hints.  You spent every weekend making him homemade pie, going on supply runs, kept the bunker clean, sit and clean guns with him.  So many damn hints.  And sure, Dean flirted with you, you were an attractive woman, but it wasn’t the way you wanted.  It wasn’t that type of attraction you wanted from Dean.  You wanted that attraction where he couldn’t keep his hands off you, but it was more than physical, he could care of you, he would want you. 

 

You knew after a while that it wasn’t happening, and deep down you were okay with it.  Because you still got to spend time with him, he was one of your best friends.  And after all these years, it didn’t really bother you until tonight. 

 

You, Sam, Dean, and Cas went out for a few drinks, hanging out at the bar, when all of a sudden, Castiel looks at you and asks, “I don’t understand the complexities of human relationships.”

 

You gave Castiel a questioning glance as he pointed over to Dean, who was playing tonsil hockey with a skinny blonde.  “Why does Dean do it with that woman when he doesn’t really care for her?”

 

Those words struck your heart and you looked away.  You sighed, and just answered your friend.  “I don’t know, Cas.  Mystery of humans, I guess.”  You turned your attention to your drink and downed a large gulp of whiskey.  You felt Sam pat your shoulder, he knew how you felt about Dean.  And to be honest, he had been urging you to tell Dean your feelings, but you didn’t want to risk ruining everything.  You had been hunting with them for so long, you didn’t think you could go back to solo.  So, you just played the good little girl and kept your mouth shut and did your job, that’s life. 

 

But it was something in the way Cas asked you that was sticking in your mind.  Maybe a distraction is what you needed, maybe answering his question would provide that distraction.  You looked up at the angel and asked.  “Cas, have you really never been in a relationship before?  With anyone?”

 

He gave you a stern look, answering in only a way that Castiel could.  “Well, I have a relationship with my brothers, and you and Sam and Dean…”

 

“No, no…Not like that, Cas.  Like a date.  Have you ever been on a date?”

 

“No, I have not.” 

 

It kinda broke your heart a little bit.  Cas was a nice guy, he deserved some fun.  So you smiled at him and said, “Well, Cas…why don’t you find a girl here and ask her on a date?” 

 

“I do not think that would wise.  I do not know these women.  I do not understand the complexities of human dating systems.”

 

Had you been paying attention, you would have noticed Sam’s grin go from one of ‘aww, cas…’ to ‘oh, do I have a plan to rock all plans.’  “Why don’t you go out on a date with Bev?” Sam asked.

 

“What?”  You shouted at him.  “Sam, knock it off!”

 

“No, I’m serious.  He says he can’t ask these women out because he doesn’t know them and doesn’t understand how to date…but he knows you, he could take you out and you can explain to him how to date.” 

 

You looked over to Castiel questioningly and saw a small smile on his face.  “I would be honored to take you out on a date, Bev.  I would be happy to learn how to date from you.” 

 

You gave an exasperated sigh as you agreed to let Castiel take you on a date.  “Alright, but I am not planning anything.  That’s the guy’s job, Sam can help you with that.” 

 

Castiel nodded and gave you a soft smile.  “Thank you for being my teacher, Bev.” 

 

And you chuckled before taking another sip of your whiskey.  At this point, Dean had shuffled back over to your table and plopped down in his seat, nudging you.  “How is it going, Bev?”  He gave you that Winchester smile, the one that made you melt on the inside.  You couldn’t help but notice…he hadn’t been going home with women like he used to.  He may have some make out sessions, but nothing past that…was he feeling alright?

 

000

 

Castiel had contacted you a couple days later and informed you that he would like to take you out on a date, picking you up at 6:00 sharp, and to wear something comfortable and warm.  You sighed when he said that and agreed, not really wanting to go out at all, but he was your friend.

 

The clock was ticking away that night and you decided it was time to get ready.  At first, you figured doing the ‘friend’ thing and going through the motions, but you know what, this was Castiel’s first date!  You didn’t want to half ass it, he was a good friend to you, you could do this for him.  So you slammed the lore book down and stood up from the desk and you looked over to Sam.

 

“Hey, Sam?  Do you mind if I borrow one of your flannels?” 

 

Sam looked up and gave you a small smile.  “Yea, sure.  Which one do you want?” 

 

“Uh, that red one would actually be perfect.  It would match my boots.” 

 

Dean chuckled from his spot, “You’re matching your boots to Sam’s flannel now?  Where the hell are you going tonight?”  His voice was light and happy, not realizing that his mood was about to change. 

 

Before you could answer, Sam’s eyes lit up as he muttered, “Oh…you’re hot date with Castiel’s tonight isn’t it?!” 

 

You blushed a little at Sam’s words.  Hot date and Castiel in the same sentence with you in context didn’t seem right…but you nodded.  You agreed, this was Cas’ first date, you were gonna put in your all.  That’s what you do for friends.

 

Dean stuttered as if he had chocked on air.  “I’m sorry, what?”

 

“Uh, yea.  I have a date with Cas tonight.  I don’t know where he is taking me, though.”  You sighed as you started to step away.  “Well, I’m gonna go get ready.  Doll myself up for my big hot date!”  You meant it sarcastically but it didn’t really come out that way, at least not to Dean’s ears.

 

He watched after you as you turned the corner and walked off to your room. 

 

“Dude, tell me she’s joking.”  Dean asked his brother seriously.

 

“What are you talking about, Dean?”

 

“She’s joking right, she isn’t really going on a date with Cas…” 

 

“No, she really is.  I was there when he asked her.”  Sam said flatly.  He knew the real reason for the date, but he also knew some other interesting details that he decided to have some fun with. 

 

“But…”  Dean pouted a little bit as he stared at the door you walked out through. “Cas doesn’t even like her!  Not like that!”

 

“How would you know who Cas likes?”  Sam deadpanned, seeing through his brother’s rouse.  “Don’t tell me you’re jealous.” 

 

“Pfft…what…uh…no!”  And without any other words, Dean slammed his book shut and stormed off towards his room.  As he walked, he began to think over everything that just happened.  Castiel was taking you for a date, you beautiful, amazing hunter, one of his best friends, out on a date.  Good for you, he thought in his mind.  Granted, he didn’t mean it to have such a bite, filled with venom, as it was. 

 

He sighed when he got to his room and slouched down on his bed.  Why were you going out with Cas?  Cas of all people!  Cas didn’t even like you like that!  Was Cas just using you to get experience?  Oh my God, Cas was using you to get experience!  Dean’s blood boiled with rage.  How could Cas do that? 

 

There was a flutter of wings and he looked up and saw the angel he was angry with standing before him. 

 

“Hello, Dean.  I wish to ask your advice on a sensitive issue.”

 

“Oh, yea, I bet you would.”  Dean bit out.  “What the hell do you think you are doing, taking Bev out on a date?  What, do you think this just some kick, take her out on a date and use her like that?”  He tried to stay in control of his emotions, but it wasn’t happening. 

 

Castiel gave him a worried look.  “Dean, I assure you I am not using her.  I was sincere when I asked her on this date.  I have never done this before.  I came to ask you for advice to ensure I did it properly.  Human dating is very complex.” 

 

The words sunk into Dean’s brain and he felt his heart break.  Holy shit, Cas was really taking Bev on a date.  Bev was in there, in n her room, making herself beautiful, even more beautiful than she already is for the freakin’ nerd angel, Castiel.  “I’m not the person to ask.”  Dean said sorrowfully.  He really wasn’t.  Cause maybe if he had advice for Cas he would have used it for himself…and maybe asked you on a date before someone else did.  “Go ask Sam.” 

 

Castiel opened his mouth, but shut it quickly.  “As you wish.”  He stated as he flew from the room. 

 

It was about twenty minutes later that there was a soft knock coming from his door, and he saw you standing in the doorway, smiling at him.  “Hey, Dean!”  You said cheerfully.  “Um…I have a favor to ask…”  You had this nervous smile as you held up Sam’s flannel.  “So, there is a little malfunction with your brother’s shirt…”  You wiggled two fingers through the fabric, showing holes that Sam obviously didn’t know were there, probably from different hunts you had all been on.  “You think you can help as sister out?  Do you have one I can borrow?”

 

Dean gave you a look. He noted how you had some makeup on your face, a dark red lipstick, some mascara and eyeliner made your eyes pop even more than they already did.  Your hair was styled back into a ponytail with a slight curl that made it bounce as you moved.  You had on your best pair of jeans, the ones that hugged every curve you had in a delicious way.  Then a black tank top on, that he was sure you were going to cover with a flannel. 

 

Dean sighed as he let his heartbreak set in.  “Nope, can’t help.”  Dean gritted out.  It was petty, sure.  But maybe if he kept you from getting another shirt you wouldn’t go on this stupid date with someone else…not when he was right here.

 

“Really, you have five flannels on the floor, I can’t borrow one?”  You asked with a surprised look.

 

“No!”  He yelled at you.  He saw you physically jump at his outburst and you looked down at the ground, and he regretted yelling.  He sighed.  “Bev…Bev.  I’m sorry-.”

 

“It’s fine, Dean.  I’ll just get another one from Sam.”  You answered softly, then turned and walked away. 

 

Dean just sat there with his head in his hands as you walked down the hallway and towards your date.

 

000

 

To say your date with Cas went interestingly was an understatement.  He had good intentions and heart, but he lacked on the execution.  He had actually found a local fair to take you to, something cool and different.  “This would be a great idea for a real date, Cas!” 

 

He gave you a questioning glance before saying he felt that this was a real date, which led you to explain what a date was used for and what it meant, between people who had feelings for each other and you saw Cas stiffen.  “I apologize, Bev, I did not realize that.”

 

“Oh, no, sweetie, it’s fine.”  You said softly.  “I’m happy to help, and you said you needed someone to explain this all to you.  Might as well be a friend… we are just friends, right Cas?”  Your heart began to pound as you waited for his answer…what if he really did like you and you just tanked his first date?!

 

Cas gave you a friendly smile and a pat on the arm.  “Of course, Bev, I will always be your friend.” 

 

And that was a great start to your evening that slowly turned south, in the most hilarious of ways. 

 

Once you got into the festival, Cas just stood there, unsure what to do.  So you had to walk him through the area, explaining what one would do if they were on a date.  “Well, you could play some games first?  You usually want to win the girl a prize.”  You explained. 

 

Castiel seemed to understand as he stepped up to a game booth and began to try to win you a prize.  In retrospect, you probably should have explained to him that most games are rigged so you lose a lot, but that didn’t stop Cas…

 

About an hour and half later, he finally, FINALLY won a game.  Seriously, you would think for an angel, he would have managed to get that little ring over the bottle sooner.  But when he did win, he looked to you questioningly.  “Which one would you like?”

 

“Well, Cas.  You just pick one that you think she would like.  Something that would remind her of you.” 

 

He nodded and began to look around at all the prizes on the wall until he pointed to a stuffed animal.  The man got it down and congratulated him on his victory.  To be honest, you had a feeling if Cas didn’t win this game the guy would have just given him something to get him to leave…  and then Cas presented to you, a small stuffed bee.  “This is perfect Cas, thank you.”

 

He smiled at your praise and then questioned you.  “Is this the end of the date?”

 

“Oh, no, Cas!”  You laughed happily as you put your arm through his, leading him away.  “These things usually last all night.” 

 

So, you led Cas around.  You played a few more games, Cas was not victorious, but he seemed to have a good time.  And then next came the rides…

 

Cas had never rode a roller coaster before, so you weren’t sure what you expected, but him screaming bloody murder sure wasn’t one of your possible outcomes.  You didn’t think an angel could get scared of a roller coaster.  For crying out loud, they fly at the speed of light, but that didn’t stop Cas.

 

“This is not a safe contraption, we must get off right now.”  He reached for your hand as you both went down another big hill.

 

“Do NOT fly me off of this thing!”  You screamed at him. 

 

Honestly, you had loved roller coasters, but Cas’ stress had gotten to you.  When the ride was over, you just shook your head.  “Okay, Cas…let’s not do anymore rides…ever…don’t ever get on another ride, alright?” 

 

All he could do was nod, his eyes still wide in sheer terror from the roller coaster. 

 

“Alight, let’s just get something to eat-.”

 

“But I do not require sustenance.”  He countered

 

“No, Cas…oh, Cas…you share the food with your date, that’s how it works.”

 

“But I do not require sustenance.”

 

“I know you don’t…uh..I’m just telling you how it works.” 

 

And that led you to the funnel cake incident.  Angels plus powdered sugar apparently are not a good combination, because for the rest of the night, Cas was bouncing off the walls with energy.  Suddenly, Gabriel’s personality made a lot more sense to you…

 

He was like a small child fawning over all the small things to see at the festival.  Granted, he was already a curious one, but the sugar made it ten times worse.  By the time the night was done, you had been laughing so hard at all the little things that went wrong, all piled up.  Him freaking out on the roller coaster, him losing at all the games, him accidently inhaling powdered sugar, his argument with a child over the proper way to play games, claiming the child cheated…

 

And when he flew you back to the bunker, you couldn’t help but lose yourself in laughter.  You landed in the library as you curled over in laughter.  Sam and Dean just watched you in curiosity.  “Oh my god!”  You said wheezing for air.  “Oh…Cas, that was one of the most fun dates I have had in a long time!” 

 

Castiel beamed at you.  “So the date was successful then?”  You just nodded your head as you laughed even harder.

 

“Even though things went wrong, it was funny, and that can make for a great date!”

 

“Very well, thank you for the date, Bev.  I hope you had a good night.”

 

“I did, Cas. Thank you.”  You waved the small bee in the air and gave him a quick kiss on the cheek.  “Thank you for tonight.” 

 

And with that, Castiel was gone.  You scooted over and collapsed into the chair next to Dean and started giggling.  “Oh, man…that was rough…so did you know Cas is scared of roller coasters?”

 

“What?”  Sam asked wide eyed.

 

“Yea!  He completely freaked out!” 

 

You and Sam shared a few bits like this, conversing about your night while Dean sat there in silence.  You really did seem like you had a good time on the date.  But when you told him about the small stuffed animal Cas had won you, how you held it close, all he could do was sigh and go off towards his room.

 

“What’s up with Dean?”

 

“I think you should talk with him.  He has been a little out of it, but I bet you could get it out of him.”  He said with a soft smile.

 

You nodded as you got up and took off after him, leaving Sam sitting there grinning like the Cheshire cat. 

 

You gave a couple knocks on Dean’s door, it was unusual to see it closed like this. 

 

“Dean, it’s me.  Can I come in?”

 

“It’s open.”  You heard answer dully.  His voice seemed really sad and depressed, it made your heart ache for him.  You hated when he was sad, so you made it your mission to cheer him up.  To cheer up the man you loved.

 

“Hey, wanna talk about it?”

 

“No, Bev, it’s fine.”  He saw that little stuffed bee still in your hand and shook his head. 

 

“Yea, it’s corny isn’t it?”  You joked.  “I had to actually explain the purpose of giving a girl a stuffed animal was…I had to explain every step, it was kinda exhausting.”

 

“Yea…I’m sure he was exhausting!”  He snapped back

 

“Excuse me?” You didn’t like his tone.  It was clear he was mad at you about something, between now and earlier with the flannel, something was bothering him. But you had done nothing wrong.  “What does that mean, Winchester?”

 

“Nothing.”  He sighed.  “Nothing, I’m just tired and I want to go to bed, can you go?” 

 

You crossed your arms and leaned against the door.  “I’m not leaving until you tell me what is wrong.”

 

“Fine, just stand there all night then.”  He barked out as he rolled over, taking the covers with him and shut out the light, going through the motions of sleep, even though he was still wearing his jeans and t-shirt. 

 

But you were too stubborn to give in, so you leaned against the doorframe.  You knew eventually he would give in and talk with you…because he hated having people watch him sleep, Cas taught you that.  So if you stood here long enough, he would feel your eyes on him…and he would get nervous, and he would finally crack.

 

“Alright, fine! You want to talk about it! How about you went on a damn date with Cas, I didn’t even know you liked Cas!”  He screamed

 

“Yea, Dean, I went on a date with Cas, but it’s not a big deal!” 

 

“No big deal?  You are starting a relationship with Cas!”  He shouted as he flipped the lights back on.

 

Your eyes went wide at his words, he didn’t really believe that did he?  Didn’t Sam tell him it was just a…sorta learning opportunity?

 

“What?”

 

“Yea…yea, Sam told me he was all over you at the bar and asked you on a date, how you were all blushing and so excited.  And you wanted to borrow his flannel so your boots and his damn shirt would match!  And his wasn’t good enough, so you had to come to me and rub it in my face.”  He was on a roll, unable to stop his emotions or his words, so he kept going.

 

“It’s bad enough that I’m in love with you, but now I have to be in love with you while you go on dates with my best friend?!”  Dean was panting, catching his breath as silence filled the room.  The reality of Dean’s words fell upon him, what he let slip, and you gasped.

 

“What did you just say?”

 

“Get out!”  He screamed.

 

“No, no, no, don’t you do that!  Don’t you drop bombs like that and just push me away!  What the hell did you just say!?”  You screamed back at him.  All the emotions the both of you had been holding in were bubbling up, ready to burst, depending on which way this conversation went. 

 

“Alright...you wanna know?  I said I was in love with you and I have to watch you date my best friend!” 

 

You couldn’t believe you just heard those words from Dean.  You took a coupe steps forward as you spoke.  “I had no idea you felt that way.” 

 

“Yea, well, now you do, so can you just leave?”

 

You sighed and set the bee aside as you sat down next to him.  “It wasn’t a real date, Dean.”

 

“What?”  The look of shock on his face rivaled the one that showed when he let it slip that he loved you.

 

“Cas asked why people make relationships so complicated.  And Sam suggested he take me on a date to learn what it was about.  That was what today was, a trial date…that frankly was…hilarious.”

 

Thinking back on that night a couple nights ago, you remembered the blonde, Dean kissing her, and you got a little angry.  “And while we are on the topic, if you love me so much, why the hell do you hook up with those girls everywhere we go?” 

 

Dean sighed as he knew this question was coming.  “Cause I can’t have you.”  He said softly.  “I hope that they will take my mind off you, but when I kiss them, I wish it was you…and then I have to stop, cause it just hurts worse…that’s why I haven’t been going home with them…it’s too much, and it’s not them I want…it’s you.”

 

“You’re too good for me, Bev.  You are one of my best friends and I can’t do that to you, I’m broken.” 

 

You had always known that Dean had this self-hated and doubt, always down on himself, but you hadn’t realized how bad it was until now.  You reached up and ran your fingers through his hair and leaned in and gave his lips a soft kiss.  “I have been in love with you for four years, Dean.  Why do you think I bake you pies every weekend or watch those stupid movies with you?”

 

Dean relaxed into your touch, letting out a happy chuckle.  “You mean we have been dancing around each other for four years?”

 

“If you’re saying how long you have been in love with me too, then I guess so.”

 

He brought his arm around you as you rested your head on his chest.  “Then let’s not waste any more time, huh?” 

 

You smiled up at him as he brought you into for a second kiss.  And behind it was all the promises and love you could muster. 

 

Out in the library sat Sam and Castiel.  They clanked two glasses together, half full with whiskey, smiles on their faces, as they finally put to rest the plan they had been working on for the past two weeks, to finally get you and Dean together. 


End file.
